Potassium Carbonate → 1-(4-methyl-2-nitro-1H-imidazol-1-yl)-3-methyl-2-butene

HRID 634897ノート

反応式

HRID 634897 の反応式
[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4]Br.C([O-])([O-])=O.[K+].[K+].[CH3:13][C:14]1[N:15]=[C:16]([N+:19]([O-:21])=[O:20])[NH:17][CH:18]=1>CC(C)=O>[CH3:13][C:14]1[N:15]=[C:16]([N+:19]([O-:21])=[O:20])[N:17]([CH2:4][CH:3]=[C:2]([CH3:6])[CH3:1])[CH:18]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 178430893HCID 178430893、化合物

生成物 1

HCID 151860141-(4-methyl-2-nitro-1H-imidazol-1-yl)-3-methyl-2-butene

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

3,3-Dimethylallyl bromide (14.08 g, 94.49 mmol) was added to a suspension of anhydrous K2CO3 (13.0 g, 94.20 mmol) and 4-methyl-2nitroimidazole (10.0 g, 78.74 mmol, D.P. Davies et al, J. Heterocyclic Chem., 1982, 19, 253-256) in dry acetone (100 mL). The reaction mixture was stirred at room temperature under nitrogen atmosphere for 15 hours. The insoluble inorganic material was removed by filtration and the filtrate was evaporated to afford a brown paste which was loaded onto a silica gel column and eluted with hexane-ethyl acetate (5:1.5). The fractions containing the compound with Rf 0.51 (silica gel TLC, hexane-ethyl acetate, 7:3) were collected and evaporated to afford a solid which was recrystallized from ethyl acetate-hexane to provide 1-(4-methyl-2-nitro-1H-imidazol-1yl)-3-methyl-2-butene as a light yellow crystalline solid in 60% (9.21 g) yield; mp. 53-54° C.; 1H NMR (CDCL3)δ1.80[s, 6H, C(CH3)2], 2.26(s, 3H, imi-CH3), 4.97(d, 2H, J=7.26 Hz, NCH2), 5.36 (t, 1H, J=7.26 Hz, CH2Ch) and 6.90(s, 1H, imi-CH). 13C NMR (CDCl3)δ 13.80(imi-CH3), 18.16 & 25.70[C(CH3)2], 47.76(NCH2), 117.35(CH2CH), 122.77(imi-CH), 138.09[C(CH3)2], 139.97(imi-CCH3) and 143.53(CNO2). MS m/e 196 (M+H)+.

後処理

  1. customThe insoluble inorganic material was removed by filtration
  2. customthe filtrate was evaporated
  3. customto afford a brown paste which
  4. washeluted with hexane-ethyl acetate (5:1.5)
  5. additionThe fractions containing the compound with Rf 0.51 (silica gel TLC, hexane-ethyl acetate, 7:3)
  6. customwere collected
  7. customevaporated
  8. customto afford a solid which
  9. customwas recrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-fc500c0f62664c399d1ae2bdcf11d3f8
出典データセット
uspto-grants-2001_02
特許番号
US06184361B2

反応ノート

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